the realisation of an ancient prophecy, which declared that, when one Hugh should succeed another Hugh immediately and lawfully as O'Donnell, the land should be freed from the yoke of the foreigner.
Sir Hugh having neglected to redeem his promise or surrender hostages for his loyalty, Perrot in September 1587 sent a vessel laden with wine round to Lough Swilly, and the master having inveigled Hugh Roe and his companions, Daniel MacSwiney and Hugh O'Gallagher, on board, under pretence of hospitality, shut the hatches on them and sailed back to Dublin. They were immediately incarcerated in Dublin Castle. Their capture caused an immense sensation, and Hugh Roe's father-in-law, the Earl of Tyrone, offered 1,000l. for his release. After lingering in prison for more than three years, Hugh Roe and his companions managed to escape early in 1591. They succeeded in reaching the Wicklow mountains; but Hugh Roe, after seeking shelter with Phelim O'Toole at Castlekevin, was recaptured and carried back to Dublin. This time extra precautions were taken for his safe custody; but, though heavily ironed, he was able, with the help of a file and a long silken rope secretly conveyed to him, to effect his escape and that of his fellow-prisoners, Henry and Art O'Neill, the sons of Shane O'Neill [q. v.], on Christmas-eve 1591. After two days' wandering among the mountains and exposure to intense cold, they were discovered by friends almost within sight of Ballinacor. Art O'Neill died from the effects of his privations, but Hugh revived sufficiently to be removed to a solitary house in the woods of Glenmalure, where he was affectionately nursed.
The news of his escape was soon noised abroad, and, a messenger from the Earl of Tyrone arriving to escort him home, he passed the Liffey near Dublin, avoiding Drogheda, and, taking the high road through Dundalk, reached Dungannon in safety. After resting there for a few days he was escorted by Hugh Maguire [q. v.] to Ballyshannon on the confines of his own country. His old rival, Hugh MacDeaganach, was no longer alive, having been murdered at the instigation of Ineenduv; but the country was torn with dissensions and entirely at the mercy of Turlough Luineach O'Neill [q. v.] and an English garrison at Donegal under Captain Willis, who kept Sir Hugh ‘as a thrall or vassal to be, as it were, a guide for him in the country.’ With the help of a few faithful followers, Hugh Roe at once marched to Donegal and expelled Willis and his soldiers. But the pain in his feet, which had been badly frost-bitten during his escape, increasing, he returned to Ballyshannon, and, by the advice of his physicians, submitted to have his great toes amputated. The operation afforded him relief, but it was many months before he was completely cured. As soon as he was able to leave his bed he summoned a meeting of the clan to Kilmacrenan at the beginning of May, and, his father having voluntarily surrendered the chieftaincy in his favour, he was inaugurated O'Donnell with the customary ceremonies, though not without signs of dissatisfaction on the part of his cousin, Niall Garv O'Donnell [q. v.]
Taking advantage of the occasion, he immediately invaded the territory of Turlough Luineach O'Neill; but fearing lest his conduct might provoke the lord deputy, Sir William Fitzwilliam [q. v.], to retaliatory measures, he despatched letters to the state explaining his election as O'Donnell and his reasons for invading Turlough Luineach, offering, if the deputy would lend him 800l. or 900l., to repair to him in person. Fitzwilliam, who recognised the necessity of conciliating him, reprimanded him for his arrogant demeanour, but promised, if he would meet him at Dundalk by 6 July, to pardon his escape and lend him 200l. It is not likely that O'Donnell's offers were meant seriously, but, by the advice of the Earl of Tyrone, who was anxious to improve his position with the government, he yielded a reluctant consent, and on 1 Aug. arrived at Dundalk. ‘And the next day, in the afternoon, in the church there, before a great assembly, delivered his humble submission, making great show of sorrow for his misdemeanours committed, protesting hereafter to hold a more dutiful course of life, and very willingly yielded himself to be sworn to perform the several parts of his submission and certain other articles.’ His submission greatly strengthened his position in Tyrconnel, and he at once took advantage of it to crush his opponents, particularly Sir John O'Dogherty, father of Cahir [q. v.], whom he placed in confinement. But there can be no question that his submission was merely a ruse to gain time in which to perfect measures of hostility to the government. In January 1593 information reached Fitzwilliam that emissaries from the pope and king of Spain, chief among whom was Edmund Magauran [q. v.], titular primate of all Ireland, were hospitably entertained by him, and from letters preserved at Simancas (O'Clery, p. 1) it is beyond dispute that application was at this time made by him and Tyrone to Spain for assistance. In March he wrested Belleek from Hugh Duve O'Donnell, and shortly afterwards secured Bundroes, thus opening for himself a pas-
